A short and efficient synthesis of ketene O,O-and S,S-acetals under focused microwave irradiation and solvent-free conditions

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1695-1698

  Díaz Ortiz, Angel ^a   Prieto, Pilar ^a   Loupy, André ^b   Abenhaïm, David ^b  

^a UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MICROWAVE RADIATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0029981833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00110-4     Document Type: Article

References (17)

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3. For example see: (a) Bailey, W. J.; Zhou, L.-L. Tetrahedron Lett. 1991, 32, 1539;
4. (b) Trogen, L. H. Acta Chem. Scand. 1993, 47, 841;
5. (c) Argade, A.B.; Joglekar, B. R. Synth. Commun. 1993, 23, 1979 for ketene O,O-acetals;
6. (d) Okuyama, T.; Fujiwara, W.; Fueno, T. Bull. Chem. Soc. Jpn. 1986, 59, 453;
7. (e) Kolb, M. Synthesis 1990, 171;
8. (f) Bellesia, F.; Boni, M.; Ghelfi, F.; Pagnoni, U. M. Synth. Commun. 1993, 23, 3179;
9. (g) Freidanck, F.; Maddaluno, J. F.; Gaonac'h, O.; Duhamel, L. Tetrahedron Lett. 1993, 34, 3871 for S,S-acetals.
10. Díez-Barra, E.; De la Hoz, A.; Díaz-Ortiz, A.; Prieto, P. Synlett 1992, 893.
11. Caddick, S. Tetrahedron 1995, 51, 10403.
12. (a) Gedye, R. N.; Rank, W.; Westaway, K. C. Can. J. Chem. 1991, 69, 706;
13. (b) Cablewski, T.; Faux, A. F.; Strauss, C. R. J. Org. Chem. 1994, 59, 3408.
14. McElvain, S. M.; Curry, M. J. J. Am. Chem. Soc. 1948, 70, 3781.
15. Typical procedure: A cold mixture (0°C) of the halogenated acetal (2 mmol), 5% of tetrabutylammonium bromide (TBAB) (0.1 mmol), if it is necessary, and the appropiate base (see table) were introduced into a pyrex tube which was then placed in a Synthewave 402 Prolabo microwave reactor fitted with a rotational system. Microwave irradiation was carried out for the time and at the power indicated (see table). The crude reaction was purified by distillation or extraction to obtain the product.
16. Bellesia, F.; Boni, M.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron 1993, 49, 199.
17. Le Ngoc, T.; Duong-Lieu, H.; Nguyen Ba, H.; Radhakrishna, A. S.; Singh, B. B.; Loupy, A. Synth. Commun., 1993, 23, 1379.